"If I Were Mayor of Boston, I Would..."

[Anthony D'Isidoro]

"If I Were Mayor of Boston, I Would..." (David Bernstein and Jonathan Soroff, Boston: August 8, 2025

While the mayoral candidates duke it out until election day, we asked 21 prominent locals what they'd do if they ran the city.

As Boston’s mayoral candidates craft talking points and dodge tough questions on the campaign trail, we decided to skip the political theater and get right to the good stuff. What would this city actually look like if the people who live, work, and shape Boston every day got to call the shots? So we posed a simple question to more than 20 opinionated locals—everyone from tech innovators to nightlife entrepreneurs, civic leaders to comedians: If you were mayor of Boston and had a magic wand to do just one transformative thing, what would it be? No campaign promises, no donor-friendly platitudes, just pure, unfiltered vision.

The answers? A mix of the smart, the practical, and the perfectly absurd. Some want to flood-proof the city before it’s underwater. Others dream of flying cars and wine gardens in Copley Square. A few just want the T to work and the Common’s puddles to drain properly.

Here’s what Boston could become if we let the dreamers, doers, and occasional cranks take the wheel.

Create Actually Useful Classes

Paul English

Kayak Cofounder, Tech Innovator, and Embrace Boston Founder Emeritus

Jessica Rinaldi / Globe Staff

If I were mayor of Boston and had the power to do just one transformative thing, I would launch a radical reboot of the public schools, and the mission would be to prepare every student not for the past but the future—and to do it with urgency, ambition, and courage.

At the core of this reboot would be universal AI literacy. Every BPS student, from the earliest grades through graduation, would learn not just about artificial intelligence but how to harness it—how to personalize their education to accelerate their learning and keep pace in an era where machines are beginning to out-think humans. AI is not just another tool; it is the most transformational technology platform in history. Boston should be the first major city in America where every public school graduate is fluent in AI—technically, ethically, and strategically.

But it still has to go deeper. I’d eliminate curriculum that has little relevance to 99 percent of today’s jobs. In its place, we’d introduce vital courses in modern living: personal finance, nutrition, mental health, civic responsibility, and digital ethics. These are not “extras”—they’re survival skills for a complex world.

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Flood-Proof This City Already

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Priscilla Douglas
Author, Businesswoman, Civic Leader, and Board Whisperer

If a genie made me mayor and handed me a magic wand, my first wish would be to fortify Boston against the looming threats of climate change. We’re not underwater yet, but we can’t wait until we are. Even as funding for the Woods Hole Oceanographic Institute, NOAA, and critical federal research gets slashed, local innovation gives us hope. The Stone Living Lab and its partners at UMass are already building the future: natural seawalls, resilient shorelines, and climate-smart infrastructure. Let’s join them—bringing urgency, collaboration, and bold thinking to the table.

Now, all I need is the genie, a sparkly blue outfit, and the chorus of “Friend Like Me,” because with vision, investment, and a little Boston grit, this wish could come true.

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Forget Innovation—Try Execution

Boston Globe Staff

Annissa Essaibi-George
Former Mayoral Candidate and Former Boston City Councilor At-Large

I would be focused on some of the basics as a city. I would certainly focus on schools and public safety, on quality-of-life issues, and on city-based taxes. We’ve seen a real concern, and I think a looming crisis, relating to residential taxes, which have such an impact on the people who live here, especially our seniors. But we also see a looming commercial tax crisis. When we’re not focused on keeping up those basics, we get really stuck, and it can create challenges.

Basic city services are critically important to the residents of Boston, so they should be critical for any municipal leader. They affect the lives of Bostonians very personally. I would be leaning into my experiences, focusing on issues I worked on as a city councilor. Thinking about the conditions of our roads and what people are experiencing when they walk out of their homes or businesses every day. And as a former schoolteacher, I certainly would be focused on our schools, making sure that our graduates are academically, socially, and emotionally prepared to go to college or to enter the workforce.

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Wine and Dine

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Carlos Bueno
General Manager, Raffles Boston

Boston’s beer-garden scene has brought a lively new energy to the city, but one of my initiatives as mayor would be to introduce a wine garden. Ideally nestled in Copley Square (just a short stroll from my office), I imagine an elegant, year-round glass-enclosed pavilion, complete with a retractable roof to invite the breeze on temperate days. Inside, guests would relax into thoughtfully arranged lounge seating and low tables, creating an atmosphere of effortless sophistication. Naturally, I would be delighted to assist in curating the wine list, with a particular focus on single-vineyard California cabernets—celebrated for their depth, character, and sense of place. Just like Boston itself.

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Stop Building for Ghost Residents

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Martyn Roetter
Chair, Neighborhood Association of the Back Bay

The first thing I would do is separate the city’s planning department from the development agency and put it under different leadership. The planning department is key. We need a master plan for housing. There’s still this obsession with tall towers that will be high-end residences for people who, in many cases, are not full-time residents of Boston. Transportation and mobility are also critical. That would be another major charter of this planning department.

 

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End the Education Shell Game

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Larry DiCara
1983 Mayoral Candidate and Former Boston City Councilor

The biggest piece of unfinished business is the schools. The school population has gone from about 100,000 when I arrived at City Hall 53 years ago to less than 50,000. So you have a school budget that continues to go up almost in inverse relationship to the school population. And the latest statistics say that only two out of five third-graders are reading at grade level. Something’s wrong with this picture.

We keep adding on employees who don’t teach. I don’t know if that is an old-fashioned way of looking at the world, or a new way of looking at the world, but if you don’t have all of your resources in the classroom, then why have a school system? On top of that, the busing program does not integrate schools; it moves children from one part of the city to the other. I mean—it’s obscene, spending $130 million on transportation. And so I think that is the greatest unfinished business of the city. If parents don’t get their kid into a school that they think is a good school, they move, and you lose that solid middle, upper-middle class. It’s really very tragic.

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Stop Winging Boston’s Future

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Marty Walz
Interim President, Boston Municipal Research Bureau

If I were mayor, I would develop and implement a five-year citywide economic development plan for Boston.

There are three things the plan needs to do. One is maximizing our strengths, which include eds and meds, and tourism and culture. It also needs to address what isn’t working. And then, it needs to be strategic about the growth industries of the future. It would be created with an understanding of the state’s economic development plan, so Boston leverages what the state is doing.

It needs to be citywide, and each region of the city will likely need a localized set of priorities. This isn’t just about downtown, because there’s growth potential in every corner of the city. We have 31 acres in South Boston that Gillette is creating a master plan for. That is very different than what could be happening in Charlestown. It has a level of waterfront other neighborhoods don’t have. So that’s what I mean: What are the strengths of each area, what are its challenges, and what are the opportunities?

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Start Winning Again

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Jim Rooney
President and CEO, Greater Boston Chamber of Commerce

I would center economic development and competitiveness. One of my early-career mentors was Congressman Joe Moakley, and he told me that in public service, our job every day is to create jobs and put people to work. That’s the most important thing that we can do.

Massachusetts, between 2010 and 2019, was ranked 16th nationally in job growth, with 15 percent job growth. From 2019 to 2024, we’re ranked 47th, with zero job growth. Between 2023 and 2024, Boston’s employment decreased by 0.3 percent, and of major cities, we’re in 20th place in terms of job growth.

By centering economic development and competitiveness, I mean the ability to compete with other cities—not just in the United States but globally, for both business development and talent development. We’ve gotten into a bit of competitive complacency. I think we need to restart that engine to drive economic development and job growth. That helps with city finances because the city depends on commercial and residential property taxes. So for the city itself to do everything that it wants, economic development has to occur right now.

And beyond that, jobs and access to good careers are what people want. We surveyed young professionals over the past year, and about 25 percent said they don’t see themselves in Boston in five years. One of the reasons was housing costs, but the second reason was access to good career development opportunities. And as I like to say, Boston is the economic capital of not just Massachusetts but all of New England. So it matters that in Boston things are flat right now.

The phrase these days is “all of government effort.” We need to create a culture within government in which you’re telling people that this is the priority. It’s not to diminish other key public policy and priorities—I would argue that if you name one of those priorities, I’ll tell you why economic development, competitiveness, and growth will help you solve those problems. So that’s why I think it’s foundational to center it.

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Make Boston Insufferably Healthy

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Jenny Johnson
Cohost, Meet Boston with Billy & Jenny and Dining Playbook

If I were magically made mayor of Boston, I would zero in on health. A liberal administration and a little crunchy on the inside.

My first decree: Let there be more olive oil! Seed oils? Banned, along with artificial food dyes. Under my watch, olive oil and grass-fed ghee would be subsidized to make them more affordable for restaurants.

I’d triple the number of farmers’ markets and offer grants to help small farms pop up in every neighborhood. Eating locally harvested veggies and meats has enormous health benefits, but access to them is a challenge.

To ensure the health of the next generation, every student would be enrolled in “Grow Boston,” a hands-on food and farming program. Real farms, real field trips, real composting. Ultra-processed foods would be eliminated from school lunches. Mindfulness would become part of the core curriculum. Yoga. Meditation. Breath work. Picture 500 kindergartners in child’s pose on the Esplanade.

My goal would be to make Boston more calm, nourished, and centered, in body, mind, and microbiome. Namaste.

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Make the Streets Work Again

Kristina Lyons

Patrick Lyons
Cofounder, the Lyons Group

The welcome mat for automobile commuters has been pulled from Boston’s front door. That’s resulted in a traffic snarl unlike anything we’ve ever seen. Who would invest in a city that doesn’t cherish systems that seek to make its commuters, visitors, residents, and convention delegates able to get into and around the city without gridlock and wasting time in bumper-to-bumper traffic?

I would impose an immediate ban on all weekday permits for street digging and construction during business hours. It would be done in the evening, not by the choice of National Grid (overtime, of course), but our streets would work better by day. We need this to bring more people to our tall buildings (thus, more commerce and taxes). There’s no reason not to follow the lead of every mayor since Kevin White on this policy.

I’d insist that Uber and Lyft share precise data on exactly how many cars they have active on our streets at any time. They have the data available in excruciating detail, and there’s an overwhelming glut of drivers and cars clogging our streets, yet we’ve all experienced an $80 five-mile ride from Logan to the Back Bay. I would reinvent and redeploy the Hackney division in the Boston Police Department to monitor the menace that Uber and Lyft have become.

Speaking of which, illegal delivery scooters and e-bikes dominate bike lanes with little regard for direction or posted rules. Must there be a bike lane to get to the front door of every building? I would study data to determine the best and most used routes before eliminating precious parking spots needed for tax-generating, mom-and-pop businesses.

For decades, Newbury Street has been the home to dozens of hair salons, supported significantly by suburban visitors. Not all of them can afford a car service, and a cut and color cannot happen in two hours. I would permit three-hour parking on Newbury Street.

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Make the Common Uncommonly Good

Courtesy of Friends of the Public Garden

Leslie Singleton Adam
Chair, Friends of the Public Garden

I want stronger sunlight protections for public spaces, and more investment from the Parks and Recreation Department budget to make these spaces really excellent. Because, you know what, the Boston Common doesn’t look great. I’ve had the good fortune of traveling around, and I see the excellence of public spaces in other cities, and ours are not excellent.

Friends of the Public Garden cares for the Boston Common, the Public Garden, and the Comm. Ave. Mall. The Boston Common is the nation’s first public park. As we approach the 250th anniversary of the revolution, that space is really important. One of the things that has always been central to our mission is the protection of these spaces from development and overuse. With a new zoning plan that’s just been released [that would allow buildings up to 700 feet tall], we find ourselves in a position of having to advocate again.

We have a Boston Common Master Plan, a detailed document of everything, given the neglect and disinvestment, that must be done to make that park excellent. If I were mayor, I would make it a priority to invest in that space. And I would make it not only Boston’s jewel but the nation’s jewel.

We also need a vibrant, safe adjacent community downtown, which is struggling. Until we have workforce housing and affordable housing, we haven’t done our job. I love parks, but we know that to be successful, it has to be part of a community. It doesn’t stand alone.

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Don’t Give Up on Diversity

Renato Castelo / Renato Castelo

Iván Espinoza-Madrigal
Executive Director, Lawyers for Civil Rights

I would double down on civil rights protection and diversity, which are critical areas under attack from the federal government and other actors. We have an opportunity to showcase how civil rights enforcement and diversity initiatives can make a world-class city like Boston continue to play a leadership role in the movement for social justice. Boston can create a blueprint for other cities to be engaged in similar advocacy. People in public and private sectors, and across many different industries, are looking for leadership. People are hungry for innovation in these spaces.

 

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End the Great Parking Giveaway

Liz Linder

Chris Dempsey
Founding Partner, Speck Dempsey

I would establish a community transportation improvement fund and pay for it by charging for residential parking permits. Neighborhoods across the city are asking for traffic calming measures: things like speed bumps and improved crosswalks and widened sidewalks. All the things that make a neighborhood more walkable and safe. The city doesn’t have the funds to pay for all of that. Some nearby communities, in particular Cambridge and Somerville, charge for on-street parking permits, whereas Boston traditionally has not. It’s well past time for the city to charge for residential parking permits, but I think people will be more open to the idea if they feel like the funds are going to a very clear purpose. The number of residential parking permits is roughly more than 100,000 vehicles. So if you charge $40 per year, that raises 4 million bucks, which would pay for a decent amount of crosswalk painting, and what we call daylighting of intersections—making sure that vehicles aren’t parked right up against a crosswalk so it’s safer for people to cross.

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Flying Cars for the Win

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Tom Timlin
Former Boston Transportation Commissioner

I like to keep things funny. And that’s why I’d require that all cars in Boston must fly.

Then you wouldn’t have any type of congestion for any reason anywhere. So that would be my mandate, that if you’re coming into the city, your car has to fly, or you just have to leave it at home.

Everybody has a way that they want to fix traffic congestion, but I have always found that when you do one thing, it leads to something else. And what nobody talks about is driver behavior. Somebody decides to park in a no-stopping zone and run in for a cup of coffee or pick up dry cleaning. You have Uber and Lyft drivers who double park and sit in the middle of the street. You can’t have police or enforcement officers at every location. The crux of the issue is personal behavior, and you’re always going to have that type of struggle.

But if we had no cars on the streets, if they were all above us, who would notice? You can have cars going east at 3,000 feet and west at 5,000 feet. It’s all good!

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Bring the Jetsons to Boston

Eric Antoniou

Jimmy Tingle
Comedian and Founder, Humor for Humanity

I’d raise money and reduce traffic by implementing an E-ZPass for all non-residents. My voice-over would say: “Welcome to Boston! There’s a cover charge. $10 to enter. Enjoy yourself! When you want to leave, it’s 20 bucks.”

After that, we’d offer free public transportation and parking for all residents and visitors by building publicly owned 10-story community garages located in every neighborhood. The garages would be equipped with EV chargers, mechanics, inspection services, car washes, and gas pumps. On the roof, there would be a greenhouse/community garden; on the first floor, a farmers’ market.

The bike paths would also have solar-paneled roofs with gutters channeling rain into a single waterfall at the Museum of Science. The energy produced would run the lights at Fenway.

Windmills would be mounted on every traffic light to generate the power needed to run the traffic lights. My critics would taunt me: “But Mr. Mayor, what happens if the wind doesn’t blow?”

And I’ll explain, “You don’t have to stop. Welcome to Boston.”

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Carve Housing out of Old Schools

Marilyn Humphries

Vanessa Calderón-Rosado
CEO, Inquilinos Boricuas en Acción

One of my first priorities would be housing. The creation of housing is critical for the stability of families in the city and the competitive advantage to keep people here. As schools are slated to be closed because of low enrollment, I would do something similar to what is being done with office spaces: provide incentives to convert empty schools into housing. And I would look for opportunities in those conversions to give teachers preference. What a wonderful opportunity for teachers in Boston Public Schools to be able to stay within the city and to live in an old schoolhouse. For moderate-income families, converted schools could provide not only rental housing but also homeownership, giving teachers an anchor in the city and the ability to build wealth and assets through homeownership.

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Turn Tenants into Owners

Vanessa Leroy Photograph

Betty Francisco
CEO, Boston Impact Initiative

I would focus on how we make this a city where everyone can thrive in a shared future, regardless of their background, income, or immigration status. How do we bring everyone into the fold to be part of shaping the future of our city? How do we create a more inclusive city where we value more transformative opportunities for ownership? Where we’ve got more of a level playing field for small businesses? How do we create opportunity for all?

Community-owned and -led real estate development models encourage community members and tenants to be part of the ownership structure. When I first came to Boston in 1994, you could afford to buy or rent something as a young professional. It was an amazing place to live, work, and play. Today, you can work and play, but the living part is becoming more unattainable. That’s why I’m so focused on how we build resilient communities, where people get the chance to be part of building them, shaping them, and owning them.

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Build, Baby, Build

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Michael Carucci
Executive Vice President, Gibson Sotheby’s International Realty

As a real estate broker, I see how hard it is to bring thoughtful new development to life. Projects are often buried in layers of zoning variances, historical board reviews, and public meetings that drag on for years. Meanwhile, Boston needs beautiful, well-designed buildings that respect the city’s character and look forward. If we want to compete globally, we need to start building like we believe Boston’s future is worth investing in.

 

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Take Down the Velvet Rope

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David Rosenthal
Actor

I would have a day of free theater. I [was recently] in The Light in the Piazza at the Huntington. I think that theater, especially nowadays, is becoming a little inaccessible, price-wise. I think it’s important to share different creative outlets and certain stories in Boston.

 

 

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Stop the Talent Bleed

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Jacquetta Van Zandt
Cohost, Politics and Prosecco, and Vice President of Engagement, the Partnership

As a young professional in Boston, I think about reversing the brain drain. We’re watching far too many of the brightest minds walk away from the state. Educators can’t afford to live in the communities that they nurture, graduates feel like they’re forced to build their lives elsewhere, and Black and brown professionals hit what I consider invisible ceilings in industries rooted here. That’s a collective failure. It isn’t solely about economic opportunity. It’s about belonging, equity, and whether Boston is truly a city for all.

If you give your heart, your labor, and your genius to this city, Boston should invest in you, too. If I were mayor, my mission would be to make Boston a place where people don’t just come to learn; they stay to lead, grow, and thrive.

I would launch a stay-in-Boston fellowship to help recent grads build careers, not just résumés, here at home. Incentivize startups and tech hubs to prioritize local, diverse hiring because, quite frankly, talent lives here, too. And, of course, build housing that people can actually afford, especially for middle-class families, educators, and first-time buyers.

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Fix the Annoying Things

Courtesy of Beacon Hill Civic Association

Colin Zick
President, Beacon Hill Civic Association

I would fix the things that frustrate residents. Boston is not always the easiest place to live, but we choose to live here because the benefits outweigh the frustrations. But eliminating those little things can go a long way toward an overall sense of improved well-being for people in the city.

Look at what’s happened at the T. The T worked, but not well, and thanks to a real devoted effort, it’s a little bit better, and it makes people a lot happier. It has a huge impact on their well-being and their ability to come into the city and do things.

Last year, people were feeling unsafe in places downtown where they weren’t used to feeling unsafe. You could argue about whether they were literally unsafe or not, but they were feeling that way. We made a lot of progress on those public safety issues and, with a lot of collective activity, got things in a much better place quickly. That shows it can be done.

I work in the Seaport, and everybody knows that the traffic trying to get out at rush hour is ridiculous. That’s the sort of thing that makes people say, “I’ll work from home, or I’ll get a job out in the suburbs.” Or, you know, that drain in the Common that never really drains, and therefore, it’s a puddle, and I don’t want to walk in the puddle. Those things add up.